Sunday's victory was the fifth in five starts for the 7-year-old in 2008, earning him $90,000 and adding to his National Steeplechase Association season earnings record, which now totals $485,520.
Preemptive Strike led from the start, with Good Night Shirt settling in behind and trailing by four- to five-lengths.
Good Night Shirt started closing in on the 10-year-old Preemptive Strike as the field made the turn for home. As the field reached the next-to-last fence, jockey Willie Dowling started to make his move, taking Good Night Shirt to the inside, closing the gap to about two lengths.
Preemptive Strike would keep a slim lead at the last fence and held it down the stretch run. Dowling used an outside-inside move and was able to overtake the race leader and jockey Jody Petty at the wire.
"I thought, jumping the last (fence) that Preemptive Strike had me. I didn't think that we would get by him," Dowling said after winning his second Colonial Cup feature in as many years.
"Good Night Shirt, through his last races has just kind of killed everybody. Today, I didn't think that going into the last, that he was going to get it done," trainer Jack Fisher said. "I didn't think he was get it done going into the last (fence.) I thought he was done."
Best Attack was third, followed by Dark Equation and Pleasant Pick.
Darren Nagle rode Dubai to victory in the $25,000 Sport of Kings Hurdle. In the Raymond G. Woolfe Memorial, Class Bopper took the win.
Bubble Economy captured the 3 1/2-mile Springdale Open timber chase and Slip Away took the Hobkirk Hill chase. Torino Luge won a 1 1/2-mile run over the flat in an amateur jockey event.